Ethyl Acetate → 1-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea

HRID 2278947ノート

反応式

HRID 2278947 の反応式
Cl.[F:2][C:3]([F:9])([F:8])[O:4][CH2:5][CH2:6][NH2:7].[H-].[Na+].[Cl:12][CH2:13][CH2:14][N:15]=[C:16]=[O:17].CCOC(C)=O>C1COCC1>[Cl:12][CH2:13][CH2:14][NH:15][C:16]([NH:7][CH2:6][CH2:5][O:4][C:3]([F:9])([F:8])[F:2])=[O:17]

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 160352-Chloroethyl isocyanateHCID 24758Sodium hydrideHCID 448908072-(Trifluoromethoxy)ethan-1-amine hydrochloride

生成物 1

HCID 904257591-(2-Chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea収率 140%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A 0° C. suspension of 2-(trifluoromethoxy)ethylamine hydrochloride (0.308 g, 1.861 mmol) in THF (10 mL) was treated with NaH (60% in mineral oil, 0.082 g, 2.047 mmol), stirred at 0° C. for 0.5 h, treated drop-wise with 2-chloroethyl isocyanate (0.175 mL, 2.047 mmol), allowed to warm to RT and stirred overnight. The mixture was treated with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness to afford 1-(2-chloroethyl)-3-(2-(trifluoromethoxy)ethyl)urea (610 mg, 140%) containing EtOAc. 1H NMR (400 MHz, DMSO-d6): δ 6.29 (br s, 2 H), 4.04-3.97 (m, 2 H), 3.55 (t, J=6.2 Hz, 2 H), 3.33-3.24 (m, 4 H).

後処理

  1. temperatureto warm to RT
  2. stirringstirred overnight
  3. customthe solids removed via filtration
  4. concentrationthe filtrate concentrated to dryness

出典と根拠

ORDレコード
ord-6c489c2a969341599c02bd99165fbf6a
出典データセット
uspto-grants-2015_09
特許番号
US09133183B2

反応ノート

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